Annual Events & Festivals

Browse our listing of annual events and make your plans! From historic downtown Brooksville to area parks and the sparkling Gulf of Mexico coast, many events celebrate our pleasant Florida weather. Pick from a brimming buffet of culinary celebrations. Step back in time with historical re-enactments and watch demonstrations of other cultures and lifestyles. Explore your interests. Discover unique entertainment. Dance, shop, taste, look and listen throughout an eventful year here in Nature’s Place to Play.

Annual Events Guide Image


January 4, 2020

Croom Zoom Trail Run

The Croom Zoom 100K/50K/25K courses uses the extensive trails of Croom Park. The trails wind through oak hammocks on a well-defined trail that takes runners through some of the best cross-country running terrain in Florida. Tucker Hill Fire Tower Parking Lot, 26416 Croom Rd., Brooksville.

More Info

January 4-5, 2020

AKC Dog Agility Trials

Don’t miss the ultimate in competitions as the dogs and handlers perform at their highest levels. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

More Info

January 5, 2020

Spring Hill Marathon Mania / Hand Cyclists Marathon

Marathon, Half-Marathon, 10K or 5K – this Boston Marathon Qualifier is Central Florida’s first marathon race of the year. Anderson Snow Park, 1360 Anderson Snow Rd., Spring Hill.

More Info

January 9-19, 2020

Florida Gulf Coast Cluster AKC All-Breed Dog Show

Ten days of competitions featuring ten American Kennel Club All-Breed Dog Shows, two days of specialty shows, Conformation, Junior Showmanship, Obedience and Rally Trials, plus visits with the dogs and their handlers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

More Info

January 18-19, 2020

Brooksville Raid

Florida’s largest Civil War Battle re-enactment portrays the 1846 raid on Bayport with artillery demonstrations, entertainment, food, sutlers, and period music. Sand Hill Scout Reservation, 11210 Cortez Blvd. (SR-50), Brooksville.

More Info

January 24-26, 2020

Florida Agriculture & Wildlife Expo

A showcase of Hernando County’s finest agriculture, wildlife, arts, talent, and industry, plus crafts and entertainment. Brooksville-Tampa Bay Regional Airport, Runway Drive entrance (off US-41 S), Brooksville.

More Info

January 25, 2020

Hernando County Greek Festival

Enjoy Greek food and pastries, music, traditional folk dance (with lessons), a toga run, kids’ zone, cooking demonstrations, arts and craft vendors and more. Christ the Savior Greek Orthodox Church, 10401 Spring Hill Drive, Spring Hill.

More Info


February 1-2, 2020

Brooksville Native American Festival

The family-friendly festival features authentic dancing and music, artists and craftsmen from around the country, primitive skills demonstrations, and Native foods like fry bread and buffalo burgers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

More Info

February 7-8, 2020

Celtic Family Jamboree

A unique family-friendly Celtic experience sharing tradition through live performance, workshops and crafts. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

February 16, 2020

Heritage Day

A celebration of 1800’s Hernando County, including historic home tours, carriage rides, museum tours, crafts and heritage activities for all ages. May-Stringer Historical Museum, 601 Museum Court, Brooksville.

More Info

February 18-23, 2020

Florida Bluegrass Classic

Enjoy five days of live Bluegrass and Classic Country performers, including TG Sheppard, Penny Creek, Big Cypress and more! Florida Classic Park, 5360 Lockhart Rd., Brooksville.

More Info

February 22, 2020

Tin Can Tourists Winter Convention Open House

Tin Can Tourists celebrate the preservation of classic Gulfstream camping trailers and motor coaches dating from the 1940’s to the 1960’s. The TCT Open House is from 11am – 3pm. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info


March 6-8, 2020

Weeki Wachee Swamp Fest

One of the premier fine arts, crafts and music festivals in the southeast includes the Swamp Monster contest and over 140 vendors and crafters, entertainment, live bands including country, folk, and toe-tapping get-up-and-dance tunes. Linda Pedersen Park, 6300 Shoal Line Blvd., Weeki Wachee.

More Info

March 7, 2020

Long Play (LP) Race (33.3M)/ Half and Full Marathons

The races start and end at the Ridge Manor Trailhead and include portions of the Croom off-road trails and the paved Withlacoochee State Trail. Lake Townsen Regional Park, 28011 Lake Lindsey Rd., Nobleton.

More Info

March 13-15, 2020

The Will McLean Music Festival

Named for the Father of Florida Folk Music, this festival features entertainment by Florida’s singers and songwriters, including workshops, arts, crafts, poetry reading, storytelling, and children’s activities. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

March 14-15, 2020

Art in the Park: Art, Crafts & Music Festival

The Gulf Coast’s largest Art Festival with over 115 artisans participating in the annual juried show featuring fine art, fine craft, craft artist vendors, student art, and live entertainment. Tom Varn Park, 306 Darby Ln., Brooksville.

More Info

March 2020

Hernando County Chamber of Commerce Annual Golf Tournament

The Chamber Golf Tournament is the “can’t miss” golf event of the year. Each year we pick a premier first-class golf experience enhanced by interactive networking activities at each tee box. Whether you love to play or are looking for a creative way to reach Hernando County executives, the Chamber tournament is a unique opportunity for budgets of all sizes.

More Info

March 14-29, 2020

Throw Down the Mountain Disc Golf Tournament

March 14 & 15, 21 & 22, 28 & 29

Florida’s largest disc golf event. Experience the fastest growing sport in the nation! Enjoy the thrilling and challenging disc moves by the competitors in the PDGA-sanctioned Vibram Open Qualifier. If you have never watched disc golf, this is a competition not to be missed. Gran Canyon, 9020 Cooper Terrace (off Mondon Hill Rd.), Brooksville.

More Info

March 20-22, 2020

Blues Bash at The Ranch

Enjoy Hot Blues – Cool Nights at this new 3-day music festival. Music, workshops, family and dog-friendly. Choose to camp or buy a day pass at Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

March 25-29, 2020

Spring Bluegrass Festival

Enjoy four days of the best in Bluegrass music, stage shows, open mic, workshops, movies, children’s activities, and a Sunday morning Gospel Sing. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info


April 4, 2020

Croom 50M/50K/16M Fools Trail Run

The beautiful and challenging 50-mile course follows three repeat loops on the Croom Hiking Trail, through central Florida’s long leaf pines and scrub oak covered hills, past creek bottoms and cypress ponds. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

More Info

April 2-5, 2020

Stringbreak Music Festival

This multi-stage Americana music fest features Roots Rock, Alternative Country, Newgrass and Bluegrass. Camping, vendors, and well-planned activities make for a great weekend. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

April 3-11, 2020

Hernando County Fair

You know it’s Spring when the Fair is here! The whole family will enjoy exhibits, Midway rides, games, livestock shows, vendors, food and live entertainment, including evening shows. Hernando County Fairgrounds, 6436 Broad St. (US-41S), Brooksville.

More Info

April 11, 2020

Weeki Wachee Springs Easter Egg Hunt

The annual Water Egg Hunt takes place at Buccaneer Bay…be sure the kids bring their bathing suits and a basket! Weeki Wachee Springs State Park, 6131 Commercial Way, Weeki Wachee.

More Info

April 18, 2020

Mermaid Chase Paddling Race

Join the Mermaid Chase Paddling Race along our Bayport – Linda Pedersen Paddling Trail. Proceeds from the 3.5 mile race are used for marine and coastal restoration projects in Hernando County.

More Info

April 11, 2020

Hop n’ Glow Easter Egg Hunt

Share some fun after the sun with games, crafts, field activities, food vendors, free give-a-ways, and photos with the Easter Bunny. Dance the night away at the Black Light Bunny Hop! Anderson Snow Park, 1360 Anderson Snow Rd., Spring Hill.

More Info

April 25, 2020

Withlacoochee Moon River

5K, 10K & Half Marathon. Run under the moon next to the beatiful Withlacoochee River! The race will start and finish at the Ridge Manor Trailhead. Ridge Manor Trailhead, Croom Rital Road and SR 50, Brooksville.

More Info


Weekends in May

Sunflower Maze, Spring Crops and Farm Activities

Maze your way through the paths of 8 to 10-foot-tall sunflowers in search of the exit. Six acres of fun, including hay rides, picnic area, family activities and spring produce. Sweetfields Farm, 17250 Benes Roush Rd., Masaryktown.

More Info

May 2020

Cause FORE Paws Golf Tournament

Join the Humane Center of the Nature Coast for a fun-filled day of golf to benefit the animals in our care. A 9:00 am shotgun start will kick off this four-person scramble which includes contests, prizes, breakfast and lunch. Location TBA.

More Info

May 13-17, 2020

Orange Blossom Jamboree

This family-friendly music festival features an outdoor pavilion and three stages for continuous entertainment with more than 60 bands. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

May 2020

Hogan Law Charity Fishing Tournament

This annual event brings out anglers of all ages for a day of flats fishing, prizes, great food, and a silent auction, all in support of HPH Hospice. Bayport Park, 4140 Cortez Blvd., Brooksville.

More Info

May 23, 2020

Spring Lake Memorial Classic

The annual run and walk wind through scenic terrain, including a nature trail through the woods, a horse barn and up and down some challenging hills! The ARC Nature Coast, 5283 Neff Lake Rd., Brooksville.

More Info


June 6, 2020

Moon Over Croom – 21M, 14M, 7M Trail Run

Experience Croom like you never have before; running in the dark. The main day-run trail is a well-marked 7-mile loop; glow sticks will mark the course for night. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

More Info

June 27, 2020

Richloam General Store Annual Hoopla

Don’t miss the Annual Hoopla! Gather for guest speakers, live music, a bounce house and great food. Enter the raffle to win exciting prizes.

More Info


First Saturday in July

Scallop Season Opens

Grab your snorkel gear and Diver-down flag and head for the water! The much-anticipated annual scallop season opens and runs into September. Bayport Park, 4140 Cortez Blvd., Brooksville or Hernando Beach Boat Ramp, 4483 Calienta St., Hernando Beach.

More Info

July 4, 2020

Firecracker Smash ‘m Up

Celebrate America with fireworks and fun for the entire family! Come out to the fairgrounds for music, games, a Kid Zone, contests, and the Demolition Derby. Hernando County Fairgrounds, 6436 Broad St. (US-41S), Brooksville.

More Info


August 14 – 16, 2020

The Spirit of Woodstock Music Festival

Set in the rolling hills of Brooksville’s Sertoma Youth Ranch, Spirit of Woodstock Music Festival is a camping optional experience you don’t want to miss. With over 80 acres of oak trees, a creek and lake, the picturesque setting is ideal for this family – and pet-friendly – event. Camp or buy single day tickets.

More Info

August 29, 2020

Olive Grove Mill Party Weekend

Tour the Orchard, Sample Our Fresh Oil and Olive Products,  See our Mill Produce Fresh Extra Virgin Olive Oil.  Workshops! Food! Beverages! Live entertainment!

More Info

August 2020

Ernie Chatman Labor Day 5K

Run on a flat, cross country course shaded by old oak trees wrapped around McKethan Lake. Enjoy music, food, prizes, and awards for each age bracket. McKethan Lake Park, 15185 Broad St. (US-41), Brooksville.

More Info


September 21, 2019

Hispanic Heritage Festival of Hernando County

Join Hernando County’s Hispanic Heritage celebration with live bands, DJs, Kid Zone, food vendors, commercial and craft vendors, beer, wine, frozen sangria, Pina Coladas, raffles and contests. Admission is Free. The Lake House, 1202 Kenlake Ave., Spring Hill

More Info

September 19, 2020

International Coastal Cleanup Day

Join others volunteering locally and around the world to keep our coastline litter-free for wildlife habitats, fragile ecosystems and beauty. Established more than 30 years ago, the Ocean Conservancy marks the third Saturday in September to Fight for Trash Free Seas. Linda Pedersen Park, 6300 Shoal Line Blvd., Weeki Wachee

More Info


October 26, 2019

Harvest Pumpkin Festival, Arts & Crafts Show

Visit the “Punkin” Patch, taste some wine, take a walk to the vineyard or a horse-drawn carriage ride. Start your Christmas shopping. Strong Tower Vineyard & Winery, 17810 Forge Drive, Spring Hill.

More Info

October 5, 2019

Mud Endeavor, Castle Canyon

Make some new friends, achieve some new goals and create new memories! This premium course resides on over 100 acres of untouched valleys with unbeaten trails and breathtaking cliffs. Castle Canyon is the site of a rock mining operation that took place in the 1920’s. 10444 Beggs Lane, Brooksville

More Info

Weekends in October

Fall RoundUp Farm Fun

Enjoy mazes, hayrides, entertainment, family activities, storytelling, games, produce barn and more. Sweetfields Farm, 7250 Benes Roush Rd., Masaryktown.

More Info

Weekends in October

Fall Corn Maze and Farm Activities

Enjoy the corn and other mazes, hayrides, entertainment, family activities and more. Harvest Moon Farm, 15990 Stur St., Masaryktown.

More Info

October 1, 2019

Papa Joe’s Annual Pasta Fest

The first Tuesday in October, bring your appetite to the 99¢ All-You-Can-Eat pasta event with children’s activities and entertainment. Papa Joe’s Italian Restaurant, 6244 Spring Lake Hwy., Brooksville.

More Info

October 12-19, 2019

Founders’ Week Celebration

Celebrating the 163nd anniversary of the founding of Brooksville, the entire family will enjoy a variety of events throughout the week. Throughout Historic Brooksville, 20 N. Main Street Area, Brooksville.

More Info

October 11-12, 2019

Halloween Harvest Festival

Enjoy fall fun for the entire family with face painting, games, food, hay rides, costume and pet-masquerade contests, plus a haunted house. Hernando County Fairgrounds, 6436 Broad St. (US-41), Brooksville.

More Info

October 12, 2019

Cardboard Boat Race

Join or watch this annual event at Hernando Beach, with prizes and fun for all, including the coveted “Titanic Award” for the most dramatic sinking. A seafood fest follows at the Hernando Beach Yacht Club. Hernando Beach Marina, 4139 Shoal Line Blvd., Hernando Beach.

More Info

October 5, 2019

John Holmes 50K, 16M, 9M Trail Run

The John Holmes is the Grand Daddy of 50Ks being the oldest trail run in Florida. This is a classic loop course with 7 mile loops. A beautiful course that winds through the oak and scrub forest of Croom – a must for anyone looking to try a 50K. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

More Info

October 18-19 & 25-26, 2019

Halloween Haunted House

Enjoy spooky hauntings and a fun-filled evening of children’s games, face painting, story-telling, roasting marshmallows around the bonfire, and more! May-Stringer House Historical Museum, 601 Museum Court, Brooksville.

More Info

October 20, 2019

Good Neighbor Trail Ride

Discover the Good Neighbor Trail at this annual Bike Ride event. Choose the 10 mile “Out and Back” family ride or other rides of varying lengths, beginning at the 1885 Train Depot at downtown Brooksville’s Russell Street Park to the 46-mile long Withlacoochee State Trail.  The Good Neighbor Trail now connects to Florida’s famous Coast to Coast Trail.

More info

October 18-20, 2019

Camping with the Blues

Enjoy three days and three nights of “Blues Under the Stars With The Stars Of The Blues.” Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

October 19, 2019

Rocky Horror Picture Show with Live Cast at the Olive Grove Fall Harvest Festival

Enjoy a meatloaf dinner and an interactive performance of  “The Rocky Horror Picture Show.” Costumes welcome! The Olive Grove, 15016 Rester Dr., Brooksville.

More Info

October 26, 2019

Nature Coast Seafood Festival

Celebrate local fresh seafood outdoors at the beautiful coastal Linda Pedersen Park. This family-friendly event features live music, arts & crafts vendors, dragon boat racing, a rubber duck race and seafood. Linda Pedersen Park, 6300 Shoal Line Blvd., Spring Hill.

More Info


November 15, 2019

Hernando Untapped

One of the most talked about craft beer and wine festivals in the area, the event features outstanding regional craft beer and wine makers. American Aviation Flight Academy, 17076 Helicopter Dr., Brooksville.

More Info

November 8, 2019

Taste of the Fields

A fabulous feast, from appetizers to desserts, prepared from local harvests by local chefs; served on the picturesque lawn of historic Chinsegut Hill. Chinsegut Hill Retreat, 22495 Chinsegut Hill Rd., Brooksville.

More Info

November 7­-10, 2019

Riverhawk Music Festival

Four days of incredible music and entertainment, workshops and jam sessions. The eclectic array of music, includes Americana, Bluegrass, Jamgrass, Celtic, Newgrass, Cajun and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info

November 23-24, 2019

Field of Dreams Car Show

The show features street rods, rat rods, classics, four-wheel drives, modern muscle, performance vehicles and more. Plus, visit the Car Corral, swap meet, arts and crafts vendors and enjoy great food and live entertainment. Florida Classic Park, 5360 Lockhart Road, Brooksville.

More Info

November 30, 2019

Snow Bash!

Kick off the winter season right…with snow! That’s right, the Snow Bash will have snow. It will even have a dedicated sledding area.  There will be live entertainment, activities, music, games, vendors, a food court and – of course – snow! Tom Varn Park, 30 Darby Lane, Brooksville.

More Info

November 28­-30, 2019

Thanksgiving Bluegrass Festival

Enjoy Thanksgiving dinner, camping, bluegrass and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

More Info


December 7, 2019

Hilly Hundred

Join this large group of cycling enthusiasts on a challenging, invigorating group ride through Florida’s Adventure Coast’s scenic countryside. Organized by Crank Works Bicycles, this is a free (self-supported) ride with voluntary donations encouraged for different local charities.

More info

December 1, 2019

Dirthead Off-Road Duathlon

The Dirthead takes place on the exhilarating off-road trails of Croom. There is a race for all levels – Sprint Duathlon (10M bike, 3.8M run) or Middle Earth Duathlon (10M bike, 8M run, 13M bike). Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

More Info

December 5, 2019

Downtown Brooksville’s Christmas Tree Lighting and Christmas on Main Street

The Brooksville Main Street organization presents the exciting Christmas tree lighting event at 7:00pm at 20 North Main Street in historic downtown Brooksville.

More Info

December 12, 19, 20, 21, 2019

Holiday Season Carriage Rides

During four holiday evenings, enjoy traditional carriage rides around historic downtown Brooksville. View festive shops and decorations, including the spectacular 30 foot courthouse Christmas tree.  20 N. Main St., Brooksville. Reservations required.

More Info

December 7, 14 & 21, 2019

Annual Downton Abbey Christmas

Downton Abbey comes to life on Florida’s Adventure Coast where Lady Grantham will learn there is never a dull moment on a weekend in Brooksville! The Tilted Teacup Tea Room & Boutique, 103 S. Saxon Ave., Brooksville.

More Info

December 14, 2019

Kiwanis Christmas Parade

One of the largest and most colorful holiday parades in Florida kicks off at 10am, followed by special activities and shopping in the historic downtown. Historic Brooksville, 20 N. Main St., Brooksville.

More Info

December 14, 2019

May-Stringer House Night of Lights Tour

Tour this Victorian Mansion after dark, festively lit for teh holiday season. Historic Brooksville, 601 Museum Court, Brooksville.

More Info


Pin It on Pinterest